Dear Old Dad contains examples of:

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As vile as Shido was in canon, he was never shown to have attempted rape or sexual assault beyond the incident that got the Protagonist put on probation. Here he's an out-and-out Serial Rapist.

Yusuke and Haru were conceived as a result of Madarame and Kunikazu Okumura, respectively, pimping their mothers out to Shido. Haru in particular is so disgusted by her "father's" actions that she completely forgives Akechi for killing him.

Abusive Parents: In addition to his canonical horrific treatment of Akechi, Shido is also Ryuji's abusive Disappeared Dad, drove his daughter Futaba into becoming a suicidally-depressed Hikikomori to cover his own ass, and tried to kill all his bastard children.

Luke, I Am Your Father: Everyone (aside from Joker and, obviously, Morgana), but of all people Ryuji turns out to be Shido's only legitimate child.

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Make an Example of Them: The circumstances that led to Makoto's conception; Shido arranged for her mother to be abducted and brought to him as a warning to her father, who was investigating some Yakuza he was connected with. It didn't work.

My God, What Have I Done?: Akechi is genuinely horrified when he realizes his murder of Wakaba Isshiki inflicted the exact same circumstances of his awful upbringing upon Futaba.

Trophy Wife: Shido expected Ryuji's mother would be this. When she wasn't, he left.

"Well Done, Son!" Guy: Both Ryuji and Akechi were this. Too bad they got stuck with Masayoshi Shido for a dad, something Ryuji's come to understand and uses to help Akechi out of his belief that his scheme to blackmail his father into respecting him won't work.

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